Hydrochloric Acid → HCID 67071680, compound

Participants

Reaction Steps

(±)-(E)-3-[1′-Methyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (105 mg, 0.35 mmol) was hydrolyzed with HCl and AcOH following the procedure described in Example 1, Step A, giving (±)-(E)-3-[1′-methyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid (110 mg, 0.34 mmol, 98%) as a white solid (hydrochloride salt). The acid was treated with NH2OTHP according to the procedure described in Example 1, Step C, to give (E)-3-[1′-methyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (90 mg, 0.23 mmol, 68%). Finally, removal of THP protecting group following the procedure described in Example 2, Step D and purification by preparative HPLC gave (±)-(E)-3-[1′-methyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-hydroxy acrylamide (30.5 mg, 31%) as its trifluoroacetic salt.

Provenance & Evidence